Methanol → (S)-tert-butyl (1-(3-fluoro-5-iodophenyl)-2-hydroxyethyl)carbamate

HRID 595998Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=C)[CH:5]=[C:6]([I:8])[CH:7]=1.[BH4-].[Na+].C[OH:23].[NH4+].[Cl-]>C(Cl)Cl.CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][OH:23])[CH:5]=[C:6]([I:8])[CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

(R)-tert-butyl (1-(3-fluoro-5-iodophenyl)allyl)carbamate (8.89 g, 23.58 mmol) was dissolved in DCM (236 mL) and cooled to −78° C. Ozone was purged through the mixture until blue color persisted. Reaction mixture was then purged with nitrogen and NaBH4 (8.92 g, 236 mmol) was added in one portion followed by addition of MeOH (120 mL) and the mixture was agitated at same temperature for 2 h and then acetone 20 mL was added. Reaction mixture was agitated for another 1 h and then poured over saturated NH4Cl and then extracted with DCM (500 mL) and then with 3:1 CHCl3/IPA (200 mL) and the organic extracts were combined and dried (magnesium sulfate), and the solvent concentrated in vacuo and the residue purified by flash chromatography to afford 6.74 g (17.7 mmol) of (S)-tert-butyl (1-(3-fluoro-5-iodophenyl)-2-hydroxyethyl)carbamate (75%). LCMS (m/z): 326.1 (MH+-56), 0.90 min.

Workup

customOzone was purged through the mixture until blue color
customReaction mixture
additionwas added in one portion
customReaction mixture
stirringwas agitated for another 1 h
extractionextracted with DCM (500 mL)
dry with materialdried (magnesium sulfate)
concentrationthe solvent concentrated in vacuo
customthe residue purified by flash chromatography

Sources & evidence

ORD record: ord-c4c855bfa97945ccb140f19ccca90276
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242996B2

Reaction notes

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