Acetic Acid → HCID 66662118, compound

HRID 2275676Notes

Reaction equation

HRID 2275676 reaction equation
[CH3:1][C:2]([C:6]1([OH:18])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)([CH3:5])[CH:3]=[CH2:4].C(O)(=[O:21])C.O>[O-2].[Cr+6].[O-2].[O-2].C(Cl)Cl>[CH3:5][C:2]1([CH3:1])[C:6]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]2)[O:18][C:4](=[O:21])[CH2:3]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962Water2×HCID 66662607HCID 66662607, compound

Product 1

HCID 66662118HCID 66662118, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of borane-dimethyl sulfide complex (0.409 mL, 0.00460 mol) in methylene chloride (6.00 mL, 0.0936 mol) was slowly added a solution of tert-butyl 3-(1,1-dimethylprop-2-en-1-yl)-3-hydroxypyrrolidine-1-carboxylate (3.20 g, 0.0125 mol) in methylene chloride (6.00 mL, 0.0936 mol) with stirring at rt. After 2 h, the reaction mixture was slowly added to a solution of chromium(VI) oxide (7.52 g, 0.0752 mol) in acetic acid (45.00 mL, 0.7915 mol), and water (5.00 mL, 0.278 mol) at 5° C. After stirring the reaction mixture at it for 12 h, water (60 mL) and methylene chloride (30 mL) were added. The organic layer was separated and the aqueous layer was farther extracted with methylene chloride (2×30 mL). The organic layers were combined, washed with brine (2×30 mL), dried and concentrated. The residue was purified on silica gel, eluting with 0 to 50% EtOAc in hexane, to give the product. LCMS (M+Na) 292.2.

Workup

  1. stirringAfter stirring the reaction mixture at it for 12 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was farther extracted with methylene chloride (2×30 mL)
  4. washwashed with brine (2×30 mL)
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel
  8. washeluting with 0 to 50% EtOAc in hexane
  9. customto give the product

Sources & evidence

ORD record
ord-9d7e7be5352d426caef7387d92231de2
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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