(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidine → 2-(R)-(3-(R)-Formyl-4-(S)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)propionic acid, benzyl ester

HRID 1386701Notes

Reaction equation

HRID 1386701 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][NH:12][CH2:11]1)(C(C)(C)C)(C)C.O[C@@H:22]([CH2:33][CH:34]1[CH2:37][CH2:36][CH2:35]1)[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>>[CH:9]([C@@H:10]1[C@@H:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:13][N:12]([C@H:22]([CH2:33][CH:34]2[CH2:37][CH2:36][CH2:35]2)[C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])[CH2:11]1)=[O:8]

Participants

3

Reactant 2

HCID 21341073(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidineHCID 53678805Benzyl (2S)-3-cyclobutyl-2-hydroxypropanoate

Product 1

HCID 599245802-(R)-(3-(R)-Formyl-4-(S)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)propionic acid, benzyl ester

Procedure

The title compound was prepared from 3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenyl pyrrolidine (from EXAMPLE 1, Step E) and 2-(S)-hydroxy-3-(cyclobutyl)propanoic acid, benzyl ester (from EXAMPLE 25, Step A) using procedures analogous to those described in EXAMPLE 1, Steps G-I. For the title compound: 1H NMR (300 MHz) δ 1.542.08 (m, 8H), 2.31 (m, 1H), 2.75 (t, J=8.6 Hz, 1H), 2.96 (m, 1H), 3.11-3.35 (m, 4H), 3.56 (q, J=7.9 Hz, H3), 5.16 (s, 2H), 7.19-7.39 (m, 10H), 9.63 (d, J=2.2 Hz, 1H).

Sources & evidence

ORD record
ord-59b8907cc1d64ce18a0aac5a6c519bd5
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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