Pivalic acid → HCID 69853443, compound

HRID 382992Notes

Reaction equation

HRID 382992 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:10][C@H:9]([OH:11])[CH2:8][C@H:7]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:6]1)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:53](O)(=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55]>C1COCC1>[C:1]([O:4][C@H:5]1[CH2:6][C@H:7]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:8][C@H:9]([O:11][C:53](=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:10]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6417Pivalic acidHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11289225HCID 11289225, compound

Product 1

HCID 69853443HCID 69853443, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 10.67 g of (1R,3S,5S)-3-(tert-butyl-dimethyl-silanoxy)-5-hydroxy-cyclohex-1-yl acetate in 107 ml of THF was added at 22° 14.55 g of triphenylphosphine, the solution was cooled to 0° and treated dropwise with a solution of 11.81 g of diisopropyl azodicarboxylate and 5.67 g of pivalic acid in 85 ml of THF over 1 h and the solution was stirred at 0° for 1 h after which time t.l.c. showed completion of the reaction. The solution was evaporated, the residue triturated with 130 ml of hexane/AcOFt 9:1, the suspension was filtered and the filtrate evaporated. The residue was chromatographed on silica with hexane/AcOEt 30:1 to give 12.63 g of the pure (t.l.c.) title compound as a colorless oil. IR (neat): 1733s (C═O); MS (EI): 371/1 (M—H).

Workup

  1. temperaturethe solution was cooled to 0°
  2. customcompletion of the reaction
  3. customThe solution was evaporated
  4. customthe residue triturated with 130 ml of hexane/AcOFt 9:1
  5. filtrationthe suspension was filtered
  6. customthe filtrate evaporated
  7. customThe residue was chromatographed on silica with hexane/AcOEt 30:1

Sources & evidence

ORD record
ord-13cb42e2fecc42fcb651ec24db45b087
Source dataset
uspto-grants-2001_10
Patent number
US06310262B1

Reaction notes

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