Trityl chloride → (3RS,4RS,5SR)-3-hydroxy-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-5-trityloxymethyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 843441Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([CH2:14][OH:15])[CH:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[CH:18][CH:17]=2)[CH:10]([OH:36])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:37]1([C:43]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)Cl)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([CH2:14][O:15][C:43]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[CH:18][CH:17]=2)[CH:10]([OH:36])[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

Reactant 2

HCID 6456Trityl chloride

HCID 54246339(3RS,4RS,5SR)-3-hydroxy-5-hydroxymethyl-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 53659348(3RS,4RS,5SR)-3-hydroxy-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-5-trityloxymethyl-piperidine-1-carboxylic acid tert-butyl ester

Procedure

In an analogous manner to that described in Example 13 (f), by reacting (3RS,4RS,5SR)-3-hydroxy-5-hydroxymethyl-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester with triphenylchloromethane there was obtained (3RS,4RS,5SR)-3-hydroxy-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]5-trityloxymethyl-piperidine-1-carboxylic acid tert-butyl ester as a colorless foam; MS: 761 (M+NH4)+.

Sources & evidence

ORD record: ord-37a8842314164d1a9f5311dd2df41246
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376672B1

Reaction notes

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