Methanol → Ethyl acetate methanol ammonium hydroxide

HRID 1158388Notes

Reaction equation

HRID 1158388 reaction equation
[C:1]([O:5][C:6]([N:8]1C[C@@H](CN(C(C)C)C(C2C=C3C(C(C)=CN3CCCOC)=CC=2)=O)[C@H](C=O)C1)=[O:7])(C)(C)[CH3:2].[CH3:37]N.[CH3:39][OH:40].[BH4-].[Na+]>C(Cl)Cl.CO>[CH3:2][CH2:1][O:5][C:6]([CH3:37])=[O:7].[CH3:39][OH:40].[NH4+:8].[OH-:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 86622388(3S,4R)-3-Formyl-4-({isopropyl-[1-(3-methoxy-propyl)-3-methyl-1H-indole-6-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 21901312Ethyl acetate methanol ammonium hydroxide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

In a similar manner as described in Example 9 for the reaction step J, the following starting material is prepared from (3S,4R)-3-formyl-4-({isopropyl-[1-(3-methoxy-propyl)-3-methyl-1H-indole-6-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (prepared under C in example 151) (3 g, 5.4 mmol), 2N solution of methylamine in MeOH (13.5 mL, 27 mmol) and NaBH4 (0.408 g, 10.8 mmol) and purification by flash chromatography on silica gel (CH2Cl2/MeOH 90:10, then AcOEt/MeOH/NH4OH 89:10:1) to give a colorless oil. MS: 515.0 [M+H]+. ]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 ml/min): 5.41 min.

Workup

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

Sources & evidence

ORD record
ord-cbcbe8b2a55945cfb283e779f8421668
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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