Sodium borohydride → HCID 69492381, compound

HRID 1279431Notes

Reaction equation

HRID 1279431 reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH:20]([CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)[C:21](OC)=[O:22])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]>O1CCCC1CCO>[C:35]([O:34][C:32]([N:29]1[CH2:30][CH2:31][CH:26]([CH2:25][CH:20]([CH2:19][CH:16]2[CH2:17][CH2:18][N:13]([C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[CH2:14][CH2:15]2)[CH2:21][OH:22])[CH2:27][CH2:28]1)=[O:33])([CH3:38])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 18770408HCID 18770408, compound

Product 1

HCID 69492381HCID 69492381, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

Under ice cooling, calcium chloride (968 mg; 8.8 mmol) and sodium borohydride (668 mg; 17 mmol) were added to a solution in tetrahydrofuran-ethanol (9 ml-14 ml) of methyl 2,2-bis[(1-tert-butoxycarbonyl-4-piperidinyl)-methyl]acetate (1.0 g; 2.1 mmol) synthesized by the process described in Referential Example 3, and the mixture was stirred for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resultant concentrated residue was dissolved in chloroform. The solution was washed successively with 3N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 900 mg (yield: 96%) of 2,2-bis[(1-tert-butoxycarbonyl-4-piperidinyl)methyl]ethyl alcohol as a colorless oil.

Workup

  1. customsynthesized by the process
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe resultant concentrated residue was dissolved in chloroform
  4. washThe solution was washed successively with 3N hydrochloric acid
  5. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4c45b84c5c8d43a8a653084447a37c04
Source dataset
uspto-grants-2002_09
Patent number
US06448242B1

Reaction notes

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