Acetic Acid → HCID 67263730、化合物

HRID 1041680ノート

反応式

HRID 1041680 の反応式
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N+:15]([C:18]1[CH:19]=[CH:20][C:21]2[O:27][CH2:26][CH2:25][CH2:24][NH:23][C:22]=2[CH:28]=1)([O-:17])=[O:16].C(O)(=O)C.C=O>C(#N)C.O.CCOC(C)=O>[CH3:1][N:23]1[C:22]2[CH:28]=[C:18]([N+:15]([O-:17])=[O:16])[CH:19]=[CH:20][C:21]=2[O:27][CH2:26][CH2:25][CH2:24]1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 109871302,3,4,5-Tetrahydro-7-nitro-1,5-benzoxazepine

生成物 1

HCID 67263730HCID 67263730、化合物収率 89%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium triacetoxyborohydride (1.02 g, 4.82 mmol) was added to 2-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (0.312 g, 1.61 mmol) in Acetonitrile (15 mL) and Acetic acid (0.20 mL, 3.5 mmol), then 13 M of Formaldehyde in Water (0.60 mL) was added. After 45 min, the mixture was poured into 100 mL EtOAc and washed with satd. sodium bicarbonate (3×30 mL) and brine (50 mL). After drying over sodium sulfate and conc. the residue was chromatographed (ISCO, 40 g, 0-40% EtOAc:Hex) to afford 9-Methyl-2-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene as an orange solid (298 mg, 89%). 1H-NMR (CDCl3): 7.65 (d, 1H, J=8.6 Hz), 7.61 (s, 1H), 6.91 (d, 1H, J=8.6 Hz), 4.29 (t, 2H, J=5.8 Hz), 3.33 (t, 2H, J=6.0 Hz), 2.86 (t, 3H), 2.08 (tt, 2H, J=5.8, 6.0 Hz)

後処理

  1. washwashed with satd
  2. dry with materialAfter drying over sodium sulfate
  3. customconc. the residue was chromatographed (ISCO, 40 g, 0-40% EtOAc:Hex)

出典と根拠

ORDレコード
ord-a76cb9ae340d4844b3f39bed46a25510
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

反応ノート

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