Borane;tetrahydrofuran → HCID 59161747, compound

HRID 409402Notes

Reaction equation

HRID 409402 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[OH:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[C:13]1[CH:17]=[CH:16][S:15][CH:14]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 2734582[(tert-Butoxycarbonyl)amino](thiophen-3-yl)acetic acid

Product 1

HCID 59161747HCID 59161747, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (±)-2-(tert-butoxycarbonylamino)-2-(thiophen-3-yl)acetic acid in THF at 0° C. was added BH3-THF dropwise. The solution was allowed to warm to room temperature and stirred for an additional 2 hours. The solution was cooled to 0° C., quenched with AcOH (10%)/MeOH and evaporated. Column chromatography (SiO2, EtOAc) gave pure tert-butyl 2-hydroxy-1-(thiophen-3-yl)ethylcarbamate (E1).

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customquenched with AcOH (10%)/MeOH
  3. customevaporated

Sources & evidence

ORD record
ord-215d27fab930468fa1027e09737e54d9
Source dataset
uspto-grants-2014_06
Patent number
US08759388B2

Reaction notes

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