Ethyl acetate hexane → (R)-3-Cyclobutyl-2-{(S)-3-(3-fluoro-phenyl)-4-[4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-pyrrolidin-1-yl}-propionic acid

HRID 1386703Notes

Reaction equation

HRID 1386703 reaction equation
[Si](O[CH2:9][C@@H:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH2:13][NH:12][CH2:11]1)(C(C)(C)C)(C)C.O[C@@H:23]([CH2:34][CH:35]1[CH2:38][CH2:37][CH2:36]1)[C:24]([O:26]CC1C=CC=CC=1)=[O:25].[CH3:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].CCO[C:48]([CH3:50])=O>>[C:41]1([CH2:14][CH2:15][CH2:16][CH:48]2[CH2:50][CH2:13][N:12]([CH2:9][C@@H:10]3[C@@H:14]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=4)[CH2:13][N:12]([C@H:23]([CH2:34][CH:35]4[CH2:36][CH2:37][CH2:38]4)[C:24]([OH:26])=[O:25])[CH2:11]3)[CH2:11][CH2:10]2)[CH:40]=[CH:39][CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 213410713-(r)-t-Butyldimethylsilyloxymethyl-4-(s)-(3-fluorophenyl)pyrrolidineHCID 53678805Benzyl (2S)-3-cyclobutyl-2-hydroxypropanoate

Product 1

HCID 20672386(R)-3-Cyclobutyl-2-{(S)-3-(3-fluoro-phenyl)-4-[4-(3-phenyl-propyl)-piperidin-1-ylmethyl]-pyrrolidin-1-yl}-propionic acid

Procedure

The title compound was prepared from 3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-(3-fluorophenyl)pyrrolidine (from EXAMPLE 20, Step H) 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: RF: 0.60 (7:3 v/v hexane/EtOAc); 1H NMR (300 MHz) 1.57-2.08 (m, 8H), 2.29 (m, 1H), 2.73 (br t, 1H), 2.92 (m, 1H), 3.14-3.34 (m, 4H), 3.56 (br q, 1H), 5.16 (s, 2H), 6.886.99 (m, 3H), 7.20-7.39 (m, 6H), 9.62 (d, J=2.0, 1H).

Sources & evidence

ORD record
ord-199e87d9f56447faad0cd3a46abfcae8
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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