Triethylamine → HCID 59254992, compound

HRID 639507Notes

Reaction equation

HRID 639507 reaction equation
[C:1]([N:8]1[CH2:25][CH2:24][C@@:15]23[C:16]4[CH:17]=[C:18]([OH:23])[CH:19]=[CH:20][C:21]=4[CH2:22][C@@H:9]1[C@@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14]3)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[C:33](Cl)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]>C(Cl)Cl>[C:1]([N:8]1[CH2:25][CH2:24][C@@:15]23[C:16]4[CH:17]=[C:18]([O:23][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[CH:19]=[CH:20][C:21]=4[CH2:22][C@@H:9]1[C@@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14]3)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 59254973HCID 59254973, compound

Product 1

HCID 59254992HCID 59254992, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-Boc-3-hydroxymorphinan 2 (20 mg, 0.058 mmol) and triethylamine (9 μL, 0.064 mmol) in dry CH2Cl2 (1 mL) was slowly added pivaloyl chloride (8 μL, 0.064 mmol) at 0° C. and the mixture stirred for 1 h. Solvent was removed under reduced pressure. The crude product was purified on a silica gel column chromatography (5:1 n-Hexane/EtOAc) to give a colorless oil (23 mg, 92% yield): 1H NMR (300 MHz, CDCl3) 0.9˜1.7 (m, 29H); 2.34 (d, J=9.9 Hz, 1H); 2.52˜2.73 (m, 2H); 3.09˜3.17 (m, 1H); 3.73˜3.84 (m, 1H); 6.83˜6.87 (m, 1H); 6.95 (s, 1H); 7.09˜7.12 (m, 1H).

Workup

  1. customat 0° C.
  2. customSolvent was removed under reduced pressure
  3. customThe crude product was purified on a silica gel column chromatography (5:1 n-Hexane/EtOAc)

Sources & evidence

ORD record
ord-7881cfcae6d44e4c9b3911392c4e6244
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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