1-Naphthaleneethanamine → HCID 11733389, compound

HRID 1977366Notes

Reaction equation

HRID 1977366 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]1[CH:20]=O)=[O:6])[CH:2]=[CH2:3].[C:22]1([CH2:32][CH2:33][NH2:34])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=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][C@@H:10]([S:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][C@H:8]1[CH2:20][NH:34][CH2:33][CH2:32][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 208531-NaphthaleneethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 10892428HCID 10892428, compound

Product 1

HCID 11733389HCID 11733389, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(2S,4S)-2-Formyl-4-BOCsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (1) (1.84 g) in dichloromethane(20 ml) was added dropwise over 10 minutes to a mixture of 2-naphthalen-1-ylethylamine (1.0 g),. sodium triacetoxyborohydride(1.36 g) and 4A powdered molecular sieve (3.0 g) in dichloromethane (130 ml) cooled to −20° C. and stirred under an argon atmosphere. After the addition was complete the reaction was allowed to warm to ambient temperature and stirred for a further 18 hours. The molecular sieves were filtered off and the fitrate stirred with saturated aqueous sodium bicarbonate solution( 100 ml) for 5 minutes. The mixture was separated, the organic phase dried over magnesium sulphate and applied to a silica flash column which was then eluted with 1.Ethyl acetate/Hexane(50:50), 2.Ethyl acetate/Hexane(80/20), 3.Ethyl acetate to give (2S,4S)-4-BOCsulfanyl-2[(2-naphthalen-1-ylethylamino)-methyl]pyrrolidine-1-carboxylic acid allyl ester (2) (2.2 g) as a colourless gum.

Workup

  1. additionAfter the addition
  2. stirringstirred for a further 18 hours
  3. filtrationThe molecular sieves were filtered off
  4. stirringthe fitrate stirred with saturated aqueous sodium bicarbonate solution( 100 ml) for 5 minutes
  5. customThe mixture was separated
  6. dry with materialthe organic phase dried over magnesium sulphate
  7. washwas then eluted with 1

Sources & evidence

ORD record
ord-dc893b6d43bf4ab19896209518fa7105
Source dataset
uspto-grants-2001_05
Patent number
US06232338B1

Reaction notes

Loading…