Sodium borohydride → tert-Butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate

HRID 336543Notes

Reaction equation

HRID 336543 reaction equation
[O:1]=[C:2]1[CH2:15][C:4]2([CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]2)[CH2:3]1.[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH2:3][C:4]2([CH2:7][N:6]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:5]2)[CH2:15]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 52333005tert-Butyl 6-oxo-2-azaspiro(3.3)heptane-2-carboxylate

Product 1

HCID 52987765tert-Butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The process is performed according to the procedure described in Example 6, step 6.1. Starting with 1.40 g (6.63 mmol) of tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate, obtained in step 11.2., dissolved in 17 mL of methanol and 0.376 g (9.94 mmol) of sodium borohydride. After evaporating off the solvent and crystallizing from a 70/30 mixture of petroleum ether and diisopropyl ether, 1.18 g of the expected product are obtained in the form of a white powder.

Workup

  1. customobtained in step 11.2
  2. customAfter evaporating off the solvent
  3. customcrystallizing from a 70/30 mixture of petroleum ether and diisopropyl ether, 1.18 g of the expected product
  4. customare obtained in the form of a white powder

Sources & evidence

ORD record
ord-d337d2447d3940ebb486a8b56cb51bfb
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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