Methanol → Ethyl acetate methanol ammonium hydroxide

HRID 1158406Notes

Reaction equation

HRID 1158406 reaction equation
[C:1]([O:5]C([N:8]1C[C@@H](C=O)[C@H](CN(C(=O)C2C=CC(C)=[C:23]([O:28][CH2:29][CH2:30]COC)[CH:22]=2)C(C)C)C1)=O)(C)(C)C.CN.C[OH:38].[BH4-].[Na+]>CCOC(C)=O.CO>[CH3:30][CH2:29][O:28][C:23]([CH3:22])=[O:38].[CH3:1][OH:5].[NH4+:8].[OH-:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 86622392HCID 86622392, compound

Product 1

HCID 21901312Ethyl acetate methanol ammonium hydroxide

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

In a similar manner as described in Example 9 for the reaction step J, the following starting materials is prepared from (3R,4S)-3-({[4-methyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-4-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (prepared under C in example 190) (2 g, 4.2 mmol), 2N solution of methylamine in MeOH (10.5 mL, 21 mmol) and NaBH4 (0.318 g, 8.40 mmol) and purification by flash chromatography on silica gel (AcOEt/MeOH 90:10, then AcOEt/MeOH/NH4OH 89:10:1) to give a colorless oil. MS: 492.1 [M+H]+.

Workup

  1. customIn a similar manner as described in Example 9 for the reaction step J

Sources & evidence

ORD record
ord-154d0c9b9dbb459aa75149d7394d9d8a
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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