Acetic Acid → HCID 117601123、化合物

HRID 578952ノート

反応式

HRID 578952 の反応式
[F:1][C:2]1([F:16])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][NH:4][CH2:3]1.[C:17]([BH3-])#N.[Na+].C=O.C(O)(=O)C>C1COCC1.C(OCC)(=O)C.CO>[F:16][C:2]1([F:1])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:6][CH2:5][N:4]([CH3:17])[CH2:3]1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 56924440tert-Butyl 6,6-difluoro-1,4-diazepane-1-carboxylate

生成物 1

HCID 117601123HCID 117601123、化合物収率 98.6%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

Combined tert-butyl 6,6-difluoro-1,4-diazepane-1-carboxylate (49 mg, 0.207 mmol) and sodium cyanoborohydride (52 mg, 0.83 mmol) in THF (1.5 mL) and added 37% aqueous formaldehyde (0.077 mL, 1.037 mmol) and acetic acid (0.018 mL, 0.311 mmol) and then stirred at 20° C. for 16 h. Then methanol (300 uL) was added and the mixture was concentrated in vacuo to give a residue which was taken up in ethyl acetate (40 mL), washed with saturated aqueous sodium bicarbonate (50 mL) and brine, dried with magnesium sulfate and concentrated in vacuo to give the title compound (51 mg, 0.204 mmol, 98%) as a clear, colorless oil. MS: 251 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46 (s, 9 H) 2.50 (s, 3 H) 2.73 (d, J=4.8 Hz, 2 H) 2.92 (t, J=13.5 Hz, 2 H) 3.55 (d, J=4.8 Hz, 2 H) 3.75-3.94 (m, 2 H).

後処理

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give a residue which
  3. washwashed with saturated aqueous sodium bicarbonate (50 mL) and brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-21de13718b3c4e13a831828d94616203
出典データセット
uspto-grants-2015_05
特許番号
US09040522B2

反応ノート

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