Isopropanol → t-Butyl (1R,2R)-1-(2,3-dihydrobenzofuran-6-yl)-1-hydroxypropan-2-ylcarbamate

HRID 13223

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

(R)-t-butyl 1-(2,3-dihydrobenzofuran-6-yl)-1-oxopropan-2-ylcarbamate (306d, 2.21 g, 7.59 mmol) was dissolved in propan-2-ol (6.35 mL, 83.4 mmol) and toluene (10 mL). Al(OiPr)3 (0.310 g, 1.52 mmol) was added, and the reaction vessel was capped and flushed with argon. The mixture was stirred at 50° C. overnight. Then another portion of Al(OiPr)3 (330 mg) was added, and stirring was continued for 5 h. The mixture was cooled to r.t., and partitioned between aq. HCl (1N, 25 ml) and ethyl acetate (80 ml). The organic layer was separated and dried. The solvent was removed in vacuo and purified by flash chromatography on silica gel with n-heptane/ethyl acetate (6:4) to give 1.58 g (71%) of subtitle compound.

Workup

customthe reaction vessel was capped
customflushed with argon
additionThen another portion of Al(OiPr)3 (330 mg) was added
stirringstirring
waitwas continued for 5 h
temperatureThe mixture was cooled to r.t.
custompartitioned between aq. HCl (1N, 25 ml) and ethyl acetate (80 ml)
customThe organic layer was separated
customdried
customThe solvent was removed in vacuo
custompurified by flash chromatography on silica gel with n-heptane/ethyl acetate (6:4)

Sources & evidence

ORD record: ord-67a5a537560240f09f61349ff310076a
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728030B2

Linked notes

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