Borane;tetrahydrofuran → HCID 60109283, compound

HRID 222063Notes

Reaction equation

HRID 222063 reaction equation
[OH:1][CH2:2][C:3](=[N:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][OH:5].B.C1COCC1>C1COCC1>[OH:1][CH2:2][CH:3]([NH:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 60109280HCID 60109280, compound

Product 1

HCID 60109283HCID 60109283, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0 THF solution of tert-butyl 2-[2-hydroxy-1-(hydroxymethyl)ethylidene]hydrazine carboxylate (1.0 g, 4.897 mmol) was added a solution of 1M BH3-THF (10 mL) dropwise. The reaction mixture was stirred at rt for 30 min, after which time the mixture was quenched by slowly adding 5 mL of methanol. The mixture was concentrated under reduced pressure and dried to give the desired product (1.12 g, 100%). 1H-NMR (DMSO-d6) δ 8.38 (s, 1H), 7.15 (s, 1H), 4.62 (s, 1H), 4.39 (t, 1H), 3.38 (q, 4H), 3.10 (s, 1H), 1.38 (s, 9H); LCMS RT=1.16 min; [M+H]+=206.9.

Workup

  1. customafter which time the mixture was quenched
  2. additionby slowly adding 5 mL of methanol
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customdried

Sources & evidence

ORD record
ord-df9eb362acbe44e4947896a696e2c913
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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