Hydrochloric Acid → (4-Benzylmorpholin-2-yl)(cyclopropyl)methanol

HRID 30322Notes

Reaction equation

B.C1COCC1.[CH2:7]([N:14]1[CH2:19][CH2:18][O:17][CH:16]([CH:20]([CH:22]2[CH2:24][CH2:23]2)[OH:21])[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O.CO>[CH2:7]([N:14]1[CH2:19][CH2:18][O:17][CH:16]([CH:20]([CH:22]2[CH2:24][CH2:23]2)[OH:21])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Borane-THF complex (1M solution in THF, 30 mL, 30 mmol, 4.1 eq) is added slowly to a solution of 75 (1.9 g, 7.3 mmol) in THF (100 mL). The reaction is heated to 60° C. After 24 hours MeOH and hydrochloric acid (2M, excess) are added and the resulting mixture heated for one hour at the same temperature. After careful addition of saturated NaHCO3 solution and EtOAc the aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine, dried over magnesium sulphate and the solvent is removed in vacuo. Purification by ion exchange chromatography gives 76 (1.1 g, 61%). MW 247.34; C15H21NO2; LCMS (6 min method) m/z 248 [M+H]+, RT 2.48 min

Workup

temperaturethe resulting mixture heated for one hour at the same temperature
extractionis extracted with EtOAc
washThe combined organic layers are washed with brine
dry with materialdried over magnesium sulphate
customthe solvent is removed in vacuo
customPurification by ion exchange chromatography

Sources & evidence

ORD record: ord-48cfe3673d67467abfa9814c6d2feaf2
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423037B2

Reaction notes

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