Triethylamine → Benzyl 4-({(3S)-3-[(tert-Butoxycarbonyl)amino]pyrrolidin-1-yl}carbonyl)piperidine-1-carboxylate

HRID 2103396Notes

Reaction equation

HRID 2103396 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:20]1[CH2:24][CH2:23][C@H:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:21]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[C:28]([O:27][C:26]([NH:25][C@H:22]1[CH2:23][CH2:24][N:20]([C:17]([CH:14]2[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:16][CH2:15]2)=[O:19])[CH2:21]1)=[O:32])([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 57803376Benzyl 4-({(3S)-3-[(tert-Butoxycarbonyl)amino]pyrrolidin-1-yl}carbonyl)piperidine-1-carboxylateYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[(benzyloxy)carbonyl]piperidine-4-carboxylic acid (5 g, 20 mmol), tert-butyl (3S)-pyrrolidin-3-ylcarbamate (3.9 g, 21 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (9.2 g, 21 mmol), and triethylamine (3.8 g, 38 mmol) in dichloromethane (100 mL) was stirred at room temperature overnight. The reaction solution was washed with water, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel to give 7.5 g of product. MS (M+H) 432.2.

Workup

  1. washThe reaction solution was washed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-b560d7657706402a9ed57e7ba975bf11
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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