Sodium Bicarbonate → Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate

HRID 587118ノート

反応式

HRID 587118 の反応式
[O:1]=[C:2]1[CH2:5][C:4]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:3]1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[OH:1][CH:2]1[CH2:5][C:4]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:3]1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 11195798Tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

生成物 1

HCID 9834677Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate収率 57%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate (600 mg, 2.5 mmol, 1.0 equiv) in MeOH (6.0 mL) was added sodium borohydride (190 mg, 5.0 mmol, 2.0 equiv) in portions at 0° C. under nitrogen. The mixture was stirred at room temperature for 2.0 hrs. The solution was concentrated by evaporator to give the white solid. Saturated NaHCO3 solution (40 mL) was added. The aqueous phase was extracted with DCM (4×30 mL). The combined organic phase was dried over anhydrous Na2SO4, concentrated to give the crude which was purified by CombiFlash (24 g silica gel column, EtOAc/Hexane=0-60%) to afford 334 mg (yield 57%) of tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate as a white solid.

後処理

  1. concentrationThe solution was concentrated by evaporator
  2. customto give the white solid
  3. extractionThe aqueous phase was extracted with DCM (4×30 mL)
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give the crude which
  7. customwas purified by CombiFlash (24 g silica gel column, EtOAc/Hexane=0-60%)

出典と根拠

ORDレコード
ord-f8c888775fca44afa279ba566c711b7b
出典データセット
uspto-grants-2016_01
特許番号
US09226923B2

反応ノート

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