Trifluoroacetic acid → [1R,2R,3R]-2,3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)-cyclobutylamine

HRID 5952Notes

Reaction equation

HRID 5952 reaction equation
[BH4-].[Na+].FC(F)(F)C(O)=O.CO[N:12]=[C:13]1[CH2:16][C@@H:15]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C@H:14]1[CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>O1CCCC1>[CH3:34][C:31]([Si:28]([CH3:30])([CH3:29])[O:27][CH2:26][C@@H:14]1[C@H:15]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:16][C@H:13]1[NH2:12])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 86747234[2R,3R]-2,3-Bis(((1,1-dimethylethyl)di-methylsilyl)oxymethyl)cyclobutanone-O-methyl oxime

Product 1

HCID 54125376[1R,2R,3R]-2,3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)-cyclobutylamineYield 115.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 4.74 g (125 mmol) of sodium borohydride in 125 mL of tetrahydrofuran (THF) was added (slowly) 14.25 g (9.63 mL, 125 mmol) of trifluoroacetic acid (TFA), followed by 10.228 g (26.4 mmol) of [2R,3R]-2,3-Bis(((1,1-dimethylethyl)di-methylsilyl)oxymethyl)cyclobutanone-O-methyl oxime, from Step F, in 25 mL of THF. After stirring the reaction mixture at ambient temperature for 1.5 h, it was concentrated, diluted with methylene chloride and washed with brine. An emulsion developed which cleared up after filtration. The methylene chloride solution was dried overnight over anhydrous magnesium sulfate, filtered and concentrated to give 10.98 g of crude title compound which was taken on to the next step without purification; MS DCI-NH3M/Z: 360 (M+NH4)+.

Workup

  1. concentrationit was concentrated
  2. additiondiluted with methylene chloride
  3. washwashed with brine
  4. filtrationafter filtration
  5. dry with materialThe methylene chloride solution was dried overnight over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9dab2a8813514c6ebc5f9dee4fe82a4c
Source dataset
uspto-grants-1993_09
Patent number
US05246931

Reaction notes

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