N-(4-Methoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)methanamine → {(S)-6-[(4-Methoxybenzyl)(tetrahydropyran-4-ylmethyl)carbamoyl]-1,2,3,4-tetrahydro-naphthalen-2-yl}carbamic acid tert-butyl ester

HRID 77418Notes

Reaction equation

HRID 77418 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[CH:15]=[C:14]([C:19]([OH:21])=O)[CH:13]=[CH:12][C:11]=2[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][O:23][C:24]1[CH:38]=[CH:37][C:27]([CH2:28][NH:29][CH2:30][CH:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[CH:26][CH:25]=1>>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19](=[O:21])[N:29]([CH2:28][C:27]3[CH:26]=[CH:25][C:24]([O:23][CH3:22])=[CH:38][CH:37]=3)[CH2:30][CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:15]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 55211610N-(4-Methoxybenzyl)-1-(tetrahydro-2H-pyran-4-yl)methanamineHCID 66663497(S)-6-tert-butoxycarbonylamino-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 66663601{(S)-6-[(4-Methoxybenzyl)(tetrahydropyran-4-ylmethyl)carbamoyl]-1,2,3,4-tetrahydro-naphthalen-2-yl}carbamic acid tert-butyl ester

Procedure

According to method G, (S)-6-tert-butoxycarbonylamino-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid was reacted with (4-methoxybenzyl)(tetrahydropyran-4-ylmethyl)amine. The crude product was purified by chromatography on silica gel (eluent: 30% n-heptane in ethyl acetate). The product was thus obtained with the molecular weight of 508.66 (C30H40N2O5); MS (ESI): 509 (M+H+).

Workup

  1. customThe crude product was purified by chromatography on silica gel (eluent: 30% n-heptane in ethyl acetate)
  2. customThe product was thus obtained with the molecular weight of 508.66 (C30H40N2O5)

Sources & evidence

ORD record
ord-f2200fab26874cfa9ace9d431e3f0c40
Source dataset
uspto-grants-2014_09
Patent number
US08841290B2

Reaction notes

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