1,2-Dichloroethane → (3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 1592771ノート

反応式

HRID 1592771 の反応式
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:11]([OH:13])=O.Cl.[CH3:22]OCN.C(Cl)CCl.C1C=C[C:33]2[N:38]([OH:39])N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1>[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:11]([N:38]([O:39][CH3:22])[CH3:33])=[O:13]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 688607(3R)-2-[(tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 21959107Methoxymethanamine hydrochloride

生成物 1

HCID 86597541(3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate収率 71.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Boc-D-Tic-OH (14.9 g, 53.7 mmol), methoxymethylamine hydrochloride (5.24 g, 53.7 mmol), EDC (11.3 g, 59.1 mmol), HOBT (7.98 g, 59.1 mmol), DIEA (9.83 ml, 59.1 mmol) and THF (500 ml) were combined, and the resulting mixture was stirred for about 18 hours at r.t. under nitrogen. The reaction mixture was concentrated and the residue was taken up in ethyl acetate. The resulting mixture was washed with 1M HCl, saturated NaHCO3 and brine, which was then dried via filtration through phase separator paper. Removal of solvent gives a residue, which was chromatographed on silica gel using (1:1 ethylacetate /hexane) to give about 12.3 g of Boc-D-Tic-NMeOMe (Weinreb amide).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. washThe resulting mixture was washed with 1M HCl, saturated NaHCO3 and brine, which
  3. customwas then dried via filtration through phase
  4. customRemoval of solvent
  5. customgives a residue, which
  6. customwas chromatographed on silica gel using (1:1 ethylacetate /hexane)

出典と根拠

ORDレコード
ord-748448a956a34aad9fc45f7d6ef29a73
出典データセット
uspto-grants-2007_11
特許番号
US07291619B2

反応ノート

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