Piperidine → HCID 68932036, compound

HRID 32072Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=O)[CH:16]=2)[O:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:16]=2)[O:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 8082Piperidine

HCID 86598502Tert-butyl 6-formylchroman-4-ylcarbamate

Product 1

HCID 68932036HCID 68932036, compound

Procedure

The reductive amination procedure in Example 1, Step H was used to react (6-formyl-chroman-4-yl)-carbamic acid tert-butyl ester (Step E) with piperidine to provide (6-piperidin-1-ylmethyl-chroman-4-yl)-carbamic acid tert-butyl ester. The Boc group was deprotected with TFA in CH2Cl2 to provide the amine salt. The coupling procedure described in the preparation of Example 1, Step F with 3-(naphthalen-2-yl-sulfonylamino)-3-phenylpropionic acid was used to provide the title compound as a mixture of diastereomers (ca. 1:1 by 1H NMR) isolated as the HCl salt. MS (ESI) 584 (M+H)+.

Sources & evidence

ORD record: ord-f82ba1b097674a6d8e9b7dd55df731f9
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425631B2

Reaction notes

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