Triphenylphosphine → HCID 178487793, compound

HRID 1422917Notes

Reaction equation

HRID 1422917 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:15]([O:19][C:20](=[O:45])[NH:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([CH:28]([CH2:31][C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([O:42][CH3:43])[CH:40]=3)[N:35]=[CH:34][C:33]=2O)[CH2:29][OH:30])[CH2:24][CH2:23]1)([CH3:18])([CH3:17])[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:15]([O:19][C:20](=[O:45])[NH:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([CH:28]2[CH2:31][C:32]3[C:41]4[C:36](=[CH:37][CH:38]=[C:39]([O:42][CH3:43])[CH:40]=4)[N:35]=[CH:34][C:33]=3[O:30][CH2:29]2)[CH2:24][CH2:23]1)([CH3:17])([CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178487964HCID 178487964, compound

Product 1

HCID 178487793HCID 178487793, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylazodicarboxylate (0.76 g, 3.80 mmol, 1.7 eq) is added at room temperature to a stirred solution of {trans-4-[2-hydroxy-1-(3-hydroxy-6-methoxy-quinolin-4-ylmethyl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester (1.08 g, 2.26 mmol, 1.0 eq) and triphenylphosphine (1.90 g, 7.53 mmol, 3.33 eq) in tetrahydrofuran (120 mL). After 1 hour stirring at room temperature, solvent is evaporated to give a crude product that is purified by preparative HPLC to afford [trans-4-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-yl)-cyclohexyl]-carbamic acid tert-butyl ester as a white lyophilizated powder (670 mg, 71% yield).

Workup

  1. customsolvent is evaporated
  2. customto give a crude product that
  3. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-a58c4abef81f42f58cb77da2c4f79b16
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

Loading…