tert-Butyl (3R)-3-(aminomethyl)pyrrolidine-1-carboxylate → (R)-3-{[(5-bromo-4-methyl-thiophene-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1162660Notes

Reaction equation

HRID 1162660 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[Br:15][C:16]1[S:20][C:19]([C:21](O)=[O:22])=[CH:18][C:17]=1[CH3:24]>>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][C@H:3]([CH2:2][NH:1][C:21]([C:19]2[S:20][C:16]([Br:15])=[C:17]([CH3:24])[CH:18]=2)=[O:22])[CH2:4]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 1515152tert-Butyl (3R)-3-(aminomethyl)pyrrolidine-1-carboxylateHCID 218994595-Bromo-4-methylthiophene-2-carboxylic acid

Product 1

HCID 58748237(R)-3-{[(5-bromo-4-methyl-thiophene-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Procedure

57.1 Using general procedure E, (R)-3-aminomethyl-1-N-tert-butoxycarbonyl-pyrrolidine was coupled with 5-bromo-4-methyl-thiophene-2-carboxylic acid (prepared according to M. Nemec et al., Collection of Czechoslovak Chemical Communications, 1974, 39, 3527) to give (R)-3-{[(5-bromo-4-methyl-thiophene-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester. White solid. MS 403.3 ([M−H]−)

Sources & evidence

ORD record
ord-3733b80029bd47af9f44b266334bdd1e
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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