Water → 1,3-dihydro-1-hydroxy-N,3,3-trimethyl-2,1-Benzoxaborole-6-methanamine

HRID 1037098ノート

反応式

HRID 1037098 の反応式
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([CH:11]=O)[CH:9]=[CH:10][C:5]=2[C:4]([CH3:14])([CH3:13])[O:3]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH3:29][NH2:30].O>C1COCC1.C(O)(=O)C>[CH3:13][C:4]1([CH3:14])[O:3][B:2]([OH:1])[C:6]2[CH:7]=[C:8]([CH2:11][NH:30][CH3:29])[CH:9]=[CH:10][C:5]1=2

参加物

7

反応物 4

HCID 962WaterHCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866854601-Hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde

生成物 1

HCID 866854591,3-dihydro-1-hydroxy-N,3,3-trimethyl-2,1-Benzoxaborole-6-methanamine収率 75%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde (370 mg, 1.95 mmol) in THF (15 mL) at rt was added NaBH(OAc)3 (827 mg, 3.9 mmol) followed by methylamine alcoholic solution (30%, 1.0 mL). Several drops of acetic acid were added to the reaction mixture to pH of 6. The mixture was continued to stir at rt overnight. Water (20 mL) was added and the mixture was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-HPLC to give 3,3-dimethyl-6-((methylamino)methyl)benzo[c][1,2]oxaborol-1(3H)-ol (300 mg; yield 75%) as a colorless oil. MS: m/z=206.1 (M+1, ESI+).

後処理

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by prep-HPLC

出典と根拠

ORDレコード
ord-5d86c0c1fb5047c5ac43a3e2716bafeb
出典データセット
uspto-grants-2013_10
特許番号
US08546357B2

反応ノート

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