Triethylamine → (3R)-N-((S)-3-azido-1-phenylpropan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carboxamide

HRID 1254246Notes

Reaction equation

HRID 1254246 reaction equation
[OH:1][C@@:2]([C@@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([C:21](Cl)=[O:22])[CH2:16]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH3:8].[N:24]([CH2:27][C@@H:28]([NH2:36])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[N+:25]=[N-:26].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:24]([CH2:27][C@@H:28]([NH:36][C:21]([N:17]1[CH2:18][CH2:19][CH2:20][C@@H:15]([C@:2]([OH:1])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH3:8])[CH2:16]1)=[O:22])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[N+:25]=[N-:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11769078(S)-1-azido-3-phenylpropan-2-amineHCID 59383029(R)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carbonyl chloride

Product 1

HCID 59383052(3R)-N-((S)-3-azido-1-phenylpropan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carboxamideYield 109.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

A solution of (R)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carbonyl chloride (135 mg, 0.4 mmol) in CH2Cl2 (10 mL) was added to a solution of (S)-1-azido-3-phenylpropan-2-amine (156.3 mg, 0.73 mmol), triethylamine (0.6 mL, 4.3 mmol), and DMAP (16.6 mg, 0.13 mmol) in CH2Cl2. After stirring for 12 h, the reaction was taken up in CH2Cl2 (50 mL), washed with satd aq NaHCO3 (3×10 mL), and brine (3×10 mL), dried (Na2SO4), decanted, and stripped to afford (3R)-N-((S)-3-azido-1-phenylpropan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carboxamide (210.7 mg) as a brown residue (theoretical yield: 192.0 mg). MS ESI +ve m/z 502 (M+Na).

Workup

  1. washwashed with satd aq NaHCO3 (3×10 mL), and brine (3×10 mL)
  2. dry with materialdried (Na2SO4)
  3. customdecanted

Sources & evidence

ORD record
ord-46292ae3b60f4883883d2388cf4d7c7a
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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