1-Naphthalenemethanamine → HCID 86756699, compound

HRID 1977367Notes

Reaction equation

[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C@H:8]1C=O)=[O:6])[CH:2]=[CH2:3].C1(CN)C2C(=CC=CC=2)C=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH:10]([S:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of (2S,4S)-2-formyl-4-BOCsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (compound (1)) (3.11 grm. ) in dichloromethane(60 ml.) was added dropwise to a stirred mixture of of 1-naphthalenemethylamine (1.71 g), 4A molecular sieves(12 grms) and sodium triacetoxyborohydride(2.3 grms) in dichloromethane (200 ml) under an argon atmosphere at −20°. The mixture was stirred for a further 30 minutes at −20° C. and then allowed to warm to ambient temperature and stirred for a further 16 hours. The mixture was filtered and washed with aqueous sodium bicarbonate solution (2×200 ml),the organic phase further washed with water (200 ml), separated, dried over magnesium sulphate and purified by column chromatography, using ethyl acetate/hexane (30:70) as eluent to give (2S,4S)-2-{[naphthalen-1-ylmethyl]-amino)-methyl}-4-BOCsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (compound(12)) as a pale yellow oil (2.09 g).

Workup

temperatureto warm to ambient temperature
stirringstirred for a further 16 hours
filtrationThe mixture was filtered
washwashed with aqueous sodium bicarbonate solution (2×200 ml),the organic phase
washfurther washed with water (200 ml)
customseparated
dry with materialdried over magnesium sulphate
custompurified by column chromatography

Sources & evidence

ORD record: ord-56075735e01a4e0083fccd8bda3b2e8e
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06232338B1

Reaction notes

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