Triphenylphosphine → HCID 10341753, compound

HRID 641473Notes

Reaction equation

HRID 641473 reaction equation
[CH:1]1([N:6]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:9]=3[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28](O)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(O)(=O)C>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([O:17][C:14]2[CH:15]=[CH:16][C:9]3[CH2:8][CH2:7][N:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:12][CH2:11][C:10]=3[CH:13]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 99915113-Cyclopentyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-ol

Product 1

HCID 10341753HCID 10341753, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Cyclopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol (E4) (1.1 g, 4.8 mmol), 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (1.15 g, 5.7 mmol), di-tert-butyl azodicarboxylate (1.31 g, 5.7 mmol) and triphenylphosphine (1.5 g, 5.7 mmol) were stirred at room temperature for 16 hours in tetrahydrofuran (20 ml). The mixture was acidified with acetic acid and applied to a SCX ion exchange cartridge (Varian bond-elute, 10 g) and washed with methanol and then a mixture of 0.880 ammonia:methanol (1:9). The combined basic fractions were concentrated in vacuo and the resulting residue was purified by column chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90) to afford the title product (E5a); MS (ES+) m/e 415 [M+H]+.

Workup

  1. washwashed with methanol
  2. additiona mixture of 0.880 ammonia:methanol (1:9)
  3. concentrationThe combined basic fractions were concentrated in vacuo
  4. customthe resulting residue was purified by column chromatography
  5. washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (1:9:90)

Sources & evidence

ORD record
ord-fcf47faacbdd4f3aba3e888cbf7448a8
Source dataset
uspto-grants-2010_04
Patent number
US07696193B2

Reaction notes

Loading…