Sodium triacetoxyborohydride → HCID 178453913, compound

HRID 2265901Notes

Reaction equation

HRID 2265901 reaction equation
[N:1]1([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][CH:30]=O)[CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:24][CH2:25][C@H:26]([CH2:29][CH2:30][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[O:9][N:8]=3)[CH2:2][CH2:3]2)[CH2:27][CH2:28]1)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 132324753-(Piperazin-1-yl)-1,2-benzoxazoleHCID 178453924HCID 178453924, compound2×

Product 1

HCID 178453913HCID 178453913, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-piperazin-1-yl-1,2-benzisoxazole (1 g, 4.92 mmol), trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (Intermediate A) (1.3 g, 5.41 mmol), in dichloromethane (15 ml) was stirred for 15 minutes at room temperature and sodium triacetoxyborohydride (1.88 g, 8.86 mmol) was added slowly and the resulting solution was stirred for 12 hours until the TLC indicated completion of the reaction. The mixture was extracted with saturated NaHCO3-solution and two times dichloromethane. The organic layers were dried over sodium sulfate, filtrated and concentrated to dryness. The crude product was purified with column chromatography on silica gel using heptane:ethyl acetate 80:20->10:90. The product fractions were concentrated to give 1.34 g (64% yield) of a white solid. MS (m/e): 429.4 (M+H+).

Workup

  1. customcompletion of the reaction
  2. extractionThe mixture was extracted with saturated NaHCO3-solution and two times dichloromethane
  3. dry with materialThe organic layers were dried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified with column chromatography on silica gel
  7. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-a0d829c9ae874f3f95723a94f2f17bde
Source dataset
uspto-grants-2010_12
Patent number
US07858630B2

Reaction notes

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