N-Hydroxyphthalimide → tert-butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]pyrrolidine-1-carboxylate

HRID 1821816ノート

反応式

HRID 1821816 の反応式
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.O[N:15]1[C:19](=[O:20])[C:18]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]2[C:16]1=[O:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:25]=[C:16]1[C:17]2[C:18](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:20])[N:15]1[O:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1

参加物

6

反応物 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 44169391-Boc-3-pyrrolidinol

生成物 1

HCID 19691445tert-butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]pyrrolidine-1-carboxylate収率 52.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To an ice-cold solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (1.0 g, 5.5 mmol), N-hydroxyphthalimide (0.90 g, 5.5 mmol) and triphenylphosphine (1.4 g, 5.5 mmol) in THF (30 mL) was added a solution of diethyl azodicarboxylate (0.96 mL, 6.1 mmol) in THF (5 mL) dropwise. The stirred reaction mixture was allowed to warm to ambient temperature. After 3 days, most of the THF was removed under reduced pressure. The residue was partitioned between CH2Cl2 (40 mL) and H2O (30 mL). The organic layer was separated and washed with saturated NaCl (20 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (silica gel, 75:25 hexanes/EtOAc to 50:50 hexanes/EtOAc) gave tert-butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]pyrrolidine-1-carboxylate (0.96 g, 52%): 1H NMR (300 MHz, CDCl3) δ1.49 (9H, s), 1.97-2.20 (1H, s), 2.25-2.31 (1H, m), 3.53-3.78 (4H, m), 4.95-5.00 (1H, m), 7.75-7.87 (4H, m).

後処理

  1. customThe stirred reaction mixture
  2. custommost of the THF was removed under reduced pressure
  3. customThe residue was partitioned between CH2Cl2 (40 mL) and H2O (30 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated NaCl (20 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customPurification by column chromatography (silica gel, 75:25 hexanes/EtOAc to 50:50 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-88acb3bb8af345ab830194b48b408bca
出典データセット
uspto-grants-2009_10
特許番号
US07608627B2

反応ノート

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