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In the title compound, C29H23N3O4, the 2-methylpyrrolidine ring adopts a twist conformation on the N—C bond involving the spiro C atom, while the hydropyran ring adopts an envelope conformation with the methine C atom bonded to the O atom as the flap. The mean plane of the indoline-2-one ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 89.73 (8)°. The latter ring makes dihedral angles of 47.80 (8) with the naphthalene ring system and 32.38 (8)° with the hydropyran ring mean plane. There is an intra­molecular C-H...O hydrogen bond involving the indoline-2-one O atom. In the crystal, adjacent mol­ecules are linked via N—H...O hydrogen bonds, forming chains propagating along [100]. The chains are linked via weak C—H...O hydrogen bonds, forming two-dimensional networks, lying parallel to (101), and consolidated by C—H...π inter­actions.

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In the title compound, C29H27N3O5, the hydropyran ring adopts an envelope conformation with the methine C atom bearing the para-meth­oxy­benzene ring as the flap. The central pyrrolidine ring has a twist conformation on the N—C bond involving the spiro C atom. The piperidine ring adopts a chair conformation. An intra­molecular C—H...O contact closes an S(7) ring. In the crystal, inversion dimers linked by C—H...O inter­actions generate R22(18) loops and N—H...O hydrogen bonds connect the dimers into [100] chains.
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