Sodium triacetoxyborohydride → HCID 58562770, compound

HRID 1896954Notes

Reaction equation

HRID 1896954 reaction equation
[Si:1]([C:8]1[S:9][C:10]([C:13]2([OH:19])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:11][N:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O=[C:21]1[CH2:24][CH:23]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:22]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[Si:1]([C:8]1[S:9][C:10]([C:13]2([OH:19])[CH2:18][CH2:17][N:16]([CH:21]3[CH2:24][CH:23]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:22]3)[CH2:15][CH2:14]2)=[CH:11][N:12]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 23374584tert-Butyl 3-oxocyclobutylcarbamateHCID 58562500HCID 58562500, compound

Product 1

HCID 58562770HCID 58562770, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 8 mL vial, was placed a solution of 4-(2-(tert-butyldimethylsilyl)thiazol-5-yl)piperidin-4-ol (as prepared in the previous step) (80 mg, 0.27 mmol, 1.00 equiv) in dichloromethane (1 mL), tert-butyl 3-oxocyclobutylcarbamate (as prepared in Step B, 128.8 mg, 0.70 mmol, 1.00 equiv) and NaBH(OAc)3 (273 mg, 1.29 mmol, 3.00 equiv). The reaction mixture was stirred for 2 h at room temperature. The reaction was then quenched by the addition of 4 ml, of H2O. The resulting solution was extracted with 3×5 mL of DCM. The combined organic layers washed with 2×5 mL of brine, dried (Na2SO4), and concentrated under vacuum. The title compound was obtained as a yellow oil.

Workup

  1. customThe reaction was then quenched by the addition of 4 ml, of H2O
  2. extractionThe resulting solution was extracted with 3×5 mL of DCM
  3. washThe combined organic layers washed with 2×5 mL of brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a900a066a84b40eba743cdfc4f22d2a7
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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