N-Methoxy-N-methylacetamide → tert-Butyl 2-(4-acetylphenyl)morpholine-4-carboxylate

HRID 710236Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:29](=[O:31])[CH3:30]>C1COCC1>[C:29]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1)(=[O:31])[CH3:30]

Participants

Conditions

Temperature: -78 °C

Procedure

tert-Butyl 2-(4-bromophenyl)morpholine-4-carboxylate (750 mg, 2.19 mmol, CAS 1131220-82-0) in THF (6 ml) was cooled to −78° C., treated dropwise with n-butyllithium (2.05 ml, 3.29 mmol, 1.6 M solution in hexane) and stirred 1 h at −78° C. N-Methoxy-N-methylacetamide (226 mg, 2.19 mmol) was added and the mixture was stirred for 1 h at −78° C., and then allowed to warm up to −5° C. The reaction mixture was quenched by addition of saturated ammonium chloride solution (4 ml) and water (4 ml) and the resulting mixture was partitioned between water and ethyl acetate.

Workup

stirringthe mixture was stirred for 1 h at −78° C.
temperatureto warm up to −5° C
customThe reaction mixture was quenched by addition of saturated ammonium chloride solution (4 ml) and water (4 ml)
customthe resulting mixture was partitioned between water and ethyl acetate

Sources & evidence

ORD record: ord-e8f36dce21474d75927ad3cec26f6f15
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181230B2

Reaction notes

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