Triethylamine → N-Boc-3-mesyloxypiperidine

HRID 341766ノート

反応式

HRID 341766 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5456991-Boc-3-hydroxypiperidine

生成物 1

HCID 568122N-Boc-3-mesyloxypiperidine収率 96.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of the title compound of Example 1 (44.3 g, 220 mmol) and Et3N (61.4 mL, 440 mmol, 2 eq) in THF (250 mL) was added dropwise at rt (maintained by cooling from an ice bath), methanesulfonyl chloride (27.77 g, 242 mmol, 1.1 eq). The reaction mixture was stirred for 1 h at rt when TLC (solvent system C) indicated completion. The precipitated Et3NHCl was removed by filtration and the filter cake was washed with 50 mL of THF. The combined filtrate and washings were evaporated in vacuo to give the crude product as a yellow oil. This was dissolved in EtOAc/hexanes (1:2) and passed through a pad of silica gel eluting with ethyl acetate/hexanes (1:3). Evaporation of the filtrate afforded the product as a pale yellow oil (59.1 g, 96%) which crystallized on standing. Recrystallization from EtOAc/hexane (1:10) afforded an analytically pure sample of the title compound: mp 69°-70° C.; 1H-NMR (CDCl3) ∂ 4.72 (m,1H), 3.63 (m, 2H), 3.46 (m, 1H), 3.32 (m, 1H), 3.05 (s, 3H), 1.75-2.06 (complex m, 4H), 1.46 (s, 9H); CIMS (MH+ calcd for C11H21NO5S): 280. Found (MH+): 280; Anal. (calcd for C11H21NO5S): C, H, N.

後処理

  1. customThe precipitated Et3NHCl was removed by filtration
  2. washthe filter cake was washed with 50 mL of THF
  3. customThe combined filtrate and washings were evaporated in vacuo
  4. customto give the crude product as a yellow oil
  5. customEvaporation of the filtrate

出典と根拠

ORDレコード
ord-92ec9bc2db7e41a6949e652f328dbeb3
出典データセット
uspto-grants-1999_01
特許番号
US05856318

反応ノート

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