tert-Butyl carbazate → N'-(oxan-4-yl)(tert-butoxy)carbohydrazide

HRID 1522423

反応式

HRID 1522423 の反応式
[O:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[NH:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[NH2:9].C([BH3-])#N.[Na+]>CO>[O:1]1[CH2:6][CH2:5][CH:4]([NH:9][NH:8][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 70091tert-Butyl carbazateHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 45092245N'-(oxan-4-yl)(tert-butoxy)carbohydrazide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Tetrahydro-4H-pyran-4-one (9.69 g, 97 mmol) was added to a solution of 1,1-dimethylethyl hydrazinecarboxylate (14.07 g, 106 mmol) in methanol (100 mL) and stirred at room temperature for 3 h. The solvent was removed in vacuo, and the crude residue was suspended in acetic acid (140 mL). Next added sodium cyanoborohydride (6.69 g, 106 mmol) in portions over 3 minutes. The contents were stirred at room temperature for 60 h. The solvent was removed in vacuo, and the crude residue was suspended in DCM (100 mL). The reaction mixture was adjusted to pH 7 with 6N NaOH. The layers were separated, and the aq. layer extracted with DCM. The combined organic layers were washed with saturated NaHCO3, and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to afford the product as a solid, 18.4 g (88%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22 (m, 2 H), 1.39 (s, 9 H), 1.43-1.48 (m, 1 H), 1.59-1.69 (m, 2 H), 2.82-2.98 (m, 1 H), 3.20-3.32 (m, 2 H), 3.80 (d, J=11.62 Hz, 2 H), 4.36 (br. s., 1 H), 8.07-8.34 (m, 1 H).

後処理

  1. customThe solvent was removed in vacuo
  2. stirringThe contents were stirred at room temperature for 60 h
  3. customThe solvent was removed in vacuo
  4. customThe layers were separated
  5. extractionthe aq. layer extracted with DCM
  6. washThe combined organic layers were washed with saturated NaHCO3, and brine
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-bd7c8314f23d4e7fb9d8ed118b907484
出典データセット
uspto-grants-2015_07
特許番号
US09073924B2

関連ノート

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