Lithium Hydroxide → HCID 89315948, compound

HRID 1497299Notes

Reaction equation

HRID 1497299 reaction equation
[F:1][C@H:2]1[C@H:7]2[NH:8]C(=O)[O:10][C@H:6]2[CH2:5][C@H:4]([CH2:12][OH:13])[C@H:3]1[OH:14].[Li+].[OH-]>O.CO>[NH2:8][C@@H:7]1[C@H:2]([F:1])[C@H:3]([OH:14])[C@@H:4]([CH2:12][OH:13])[CH2:5][C@@H:6]1[OH:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 71152561HCID 71152561, compound

Product 1

HCID 89315948HCID 89315948, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of (3aS,4S,5R,6R,7aS)-4-fluoro-5-hydroxy-6-(hydroxymethyl)hexahydrobenzo[d]oxazol-2(3H)-one (704 mg, 3.43 mmol) and LiOH (2.71 g, 113 mmol) in water (35 mL) and MeOH (26 mL) was stirred at reflux for 2 h. The solvents were evaporated to give the crude product. This was purified by SiO2 column, eluted with 20%-30% 2 M NH3 MeOH solution in DCM give (1S,2S,3S,4R,5R)-2-amino-3-fluoro-5-(hydroxymethyl)cyclohexane-1,4-diol (485 mg, 80%) as a white solid. 1H NMR (400 MHz, MeOD) δ 4.74 (d, J=52.0 Hz, 1H), 3.96-3.99 (m, 1H), 3.65-3.73 (m, 2H), 3.49 (ddd, J=28.0 Hz, 10.5 Hz, 1.6 Hz, 1H), 3.05 (d, J=31.0 Hz, 1H), 2.09-2.19 (m, 1H), 1.96 (dt, J=14.5 Hz, 3.7 Hz, 1H), 1.46-1.53 (m, 1H).

Workup

  1. temperatureat reflux for 2 h
  2. customThe solvents were evaporated
  3. customto give the crude product
  4. customThis was purified by SiO2 column
  5. washeluted with 20%-30% 2 M NH3 MeOH solution in DCM

Sources & evidence

ORD record
ord-e69b54f4fa7c42368482c09a4e428dc9
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

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