Sodium borohydride → HCID 86596972, compound

HRID 2225298Notes

Reaction equation

HRID 2225298 reaction equation
[CH2:1]([N:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:9]1[CH2:15][CH2:14][CH:13]2[CH2:16][CH:10]1[C:11](=[O:24])[N:12]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.O>[CH2:25]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]1[CH2:15][CH2:14][C@@H:13]([NH:12][C:17](=[O:18])[O:19][C:20]([CH3:22])([CH3:23])[CH3:21])[CH2:16][C@H:10]1[CH2:11][OH:24])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 69285670HCID 69285670, compound

Product 1

HCID 86596972HCID 86596972, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Examples 11p and 11q, Step 3: To a solution of tert-butyl 2-(dibenzylamino)-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate (3.12 g, 7.42 mmoles) in 50 ml of THF and 10 ml of water was added sodium borohydride (1.4 g, 37.1 mmoles), and the mixture was stirred for 6 hours at room temperature. The reaction was quenched with saturatedd sodium bicarbonate, and the product was extracted with EtOAc three times. The combined extracts were washed with brine, dried over Na2SO4 and evaporated to give an oily residue. It was purified by column chromatography (silica gel, 3:7 EtOAc and hexane) to give 2.28 g of tert-butyl (1R,3R,4S)-4-(dibenzylamino)-3-(hydroxymethyl)cyclohexylcarbamate as an oil.

Workup

  1. customThe reaction was quenched with saturatedd sodium bicarbonate
  2. extractionthe product was extracted with EtOAc three times
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto give an oily residue
  7. customIt was purified by column chromatography (silica gel, 3:7 EtOAc and hexane)

Sources & evidence

ORD record
ord-60b09d5680d0451e82c4ebfb15f3a425
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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