Hydrochloric Acid → (S)-tert-butyl 3-(benzyloxy)-1-oxopropan-2-ylcarbamate

HRID 37041Notes

Reaction equation

C[O:2][C:3](=O)[C@H:4]([CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[H-].C([Al+]CC(C)C)C(C)C.Cl>C1(C)C=CC=CC=1>[C:6]([NH:5][C@H:4]([CH:3]=[O:2])[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([O:8][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:7]

Participants

Conditions

Temperature: -70 °C

Procedure

N-Boc-O-benzylserine methyl ester (9.5 g, 32 mmol) was dissolved in dry toluene (distilled from sodium) (100 ml). The solution was cooled to -70° C., and a solution of diisobutylaluminium hydride in toluene (1.2M, 53 ml, 64 mmol) was added dropwise over a period of 45 minutes under vigorous stirring under nitrogen. The mixture was stirred for an additional 20 minutes and was then allowed to reach -50° C. Hydrochloric acid (2M, 150 ml) was carefully added and the resulting reaction mixture was allowed to reach -10° C. The organic layer was separated and the aqueous layer was extracted with ethylacetate (2×100 ml). The combined organic solution was dried with sodium sulphate and evaporated to dryness below 40° C. (bath temperature). The N-Boc-O-benzylserinal was isolated as a colourless oil. Yield 8.6 g (96%). The structure was confirmed by 1HNMR and 13CNMR.

Workup

stirringThe mixture was stirred for an additional 20 minutes
customto reach -50° C
customthe resulting reaction mixture
customto reach -10° C
customThe organic layer was separated
extractionthe aqueous layer was extracted with ethylacetate (2×100 ml)
dry with materialThe combined organic solution was dried with sodium sulphate
customevaporated to dryness below 40° C. (bath temperature)

Sources & evidence

ORD record: ord-ecc206a2bd8c424fb0b0d9cec735a75a
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05419893

Reaction notes

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