2-Chloroethanol → (2R,3R,4R)-3,4-Dibenzyloxy-2-benzyloxymethyl-1-(2-hydroxyethyl)pyrrolidine

HRID 1459651Notes

Reaction equation

HRID 1459651 reaction equation
Cl.[CH2:2]([O:9][C@@H]1[C@H](OCC2C=CC=CC=2)CN(CC2CC2)[C@]1(C)OCC1C=CC=CC=1)[C:3]1C=CC=CC=1.[CH2:36]([O:43][C@H:44]1[C@H:48]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:47][NH:46][C@@H:45]1[CH2:57][O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.ClCCO>>[CH2:36]([O:43][C@H:44]1[C@H:48]([O:49][CH2:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH2:47][N:46]([CH2:3][CH2:2][OH:9])[C@@H:45]1[CH2:57][O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 3

HCID 342-ChloroethanolHCID 22842874(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine2×HCID 131721050(2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxy-methyl-1-cyclopropylmethylpyrrolidine, hydrochloride

Product 1

HCID 54162120(2R,3R,4R)-3,4-Dibenzyloxy-2-benzyloxymethyl-1-(2-hydroxyethyl)pyrrolidine

Procedure

The title compound was prepared as described for compound 8 using (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine (Compound 1) (0.51g, 1.27 mmol) and 2-chloroethanol (0.1ml, 1.49 mmol) as starting material. (2R,3R,4R)-3,4-Dibenzyloxy-2-benzyloxymethyl-1-(2-hydroxyethyl)pyrrolidine was obtained as a golden oil (0.48 g, yield: 85 %).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-99aa1c44ff0d4f669c7243642ca5cc08
Source dataset
uspto-grants-1998_12
Patent number
US05854272

Reaction notes

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