Hydrochloric Acid → HCID 178487964, compound

HRID 2273205Notes

Reaction equation

HRID 2273205 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH:17]2[CH2:30][C:29]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([O:31][CH3:32])[CH:27]=4)[N:22]=[CH:21][C:20]=3[O:19][CH:18]2[O:33]C(=O)C)[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl.ClCCl>C(O)C.CO>[C:3]([O:7][C:8](=[O:9])[NH:10][C@H:11]1[CH2:12][CH2:13][C@H:14]([CH:17]([CH2:30][C:29]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([O:31][CH3:32])[CH:27]=3)[N:22]=[CH:21][C:20]=2[OH:19])[CH2:18][OH:33])[CH2:15][CH2:16]1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 178487794HCID 178487794, compound

Product 1

HCID 178487964HCID 178487964, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Sodium borohydride (920 mg, 24.2 mmol, 6.0 eq) is added at room temperature to a stirred solution of acetic acid 3-(trans-4-tert-butoxycarbonylamino-cyclohexyl)-6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-2-yl ester (1.90 g, 4.04 mmol, 1.0 eq) in ethanol (120 mL). After 1 hour stirring at room temperature, the reaction mixture is acidified with a 1N hydrochloric acid aqueous solution to pH 4. Solvent is evaporated and the residue is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 25:1 to 15:1, v/v) to afford {trans-4-[2-hydroxy-1-(3-hydroxy-6-methoxy-quinolin-4-ylmethyl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid (1.26 g, 65% yield).

Workup

  1. customSolvent is evaporated
  2. customthe residue is purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-d146e6fd43b347ccb5aab2d62a875aec
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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