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

HRID 1371519ノート

反応式

HRID 1371519 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.C1C=C[C:29]2[N:34]([OH:35])N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C(OCC)(=O)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:34]([O:35][CH3:22])[CH3:29])=[O:13]

参加物

9

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 75.9%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Boc-D-Tic-OH (4.50 g, 16 mmol), methoxymethylamine hydrochloride (1.56 g, 16 mmol), HOBT (2.43 g, 18 mmol), EDC (3.45 g, 18 mmol), DMAP (200 mg, 1.6 mmol), DIPEA (4.2 ml) and THF (150 ml) are combined, and the resulting mixture is stirred for about 18 hours at r.t. The mixture is stripped to dryness, and the resulting residue is taken up in ethyl acetate and then washed with aqueous HCl (1N), aqueous sodium bicarbonate and brine, which is then dried over sodium sulfate. The solvent is removed and the residue is chromatographed on normal phase (ethylacetate/hexanes 1:1) to give about 3.89 g of Boc-D-Tic-NMeOMe (Weinreb amide).

後処理

  1. washwashed with aqueous HCl (1N), aqueous sodium bicarbonate and brine, which
  2. dry with materialis then dried over sodium sulfate
  3. customThe solvent is removed
  4. customthe residue is chromatographed on normal phase (ethylacetate/hexanes 1:1)

出典と根拠

ORDレコード
ord-fbb18be264924fb990ddf69c922decdd
出典データセット
uspto-grants-2007_01
特許番号
US07157463B2

反応ノート

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