Allyl bromide → Tert-butyl (3s,5s,6r)-3-allyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate

HRID 1743248Notes

Reaction equation

[O:1]=[C:2]1[O:7][C@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:37](Br)[CH:38]=[CH2:39].[Cl-].[NH4+]>C1COCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:39]([C@H:3]1[C:2](=[O:1])[O:7][C@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:4]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:38]=[CH2:37]

Participants

Conditions

Temperature: -78 °C

Procedure

10 g of tert-butyl (5S,6R)-2-oxo-5,6-diphenylmorpholine-4-carboxylate were dissolved in 200 ml of THF and cooled to −78° C. 63 ml of a 0.5 M solution of KHMDS in toluene were added dropwise and, after stirring for 10 min, 3.7 ml of allyl bromide were added dropwise. The mixture was allowed to warm from −78° C. to −20° C. over the course of 3 h, and the reaction was then stopped by adding 300 ml of a saturated ammonium chloride solution. 200 ml of ethyl acetate were added, and the phases were separated. The aqueous phase was extracted 3 times with 100 ml of ethyl acetate each time, and the combined organic phases were dried with MgSO4. The solvents were removed in vacuo and the residue was stirred with diisopropyl ether.

Workup

temperatureto warm from −78° C. to −20° C. over the course of 3 h
customthe phases were separated
extractionThe aqueous phase was extracted 3 times with 100 ml of ethyl acetate each time
dry with materialthe combined organic phases were dried with MgSO4
customThe solvents were removed in vacuo
stirringthe residue was stirred with diisopropyl ether

Sources & evidence

ORD record: ord-9f364c30dc6f4b19af11cf7bacabaeaa
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07008957B2

Reaction notes

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