Benzyl Alcohol → Benzyl oxolan-3-ylcarbamate

HRID 481346ノート

反応式

HRID 481346 の反応式
[O:1]1[CH2:5][CH2:4][CH:3](C(O)=O)[CH2:2]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:16])C=CC=CC=1.C([N:28]([CH2:31]C)CC)C.[CH2:33]([OH:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCOCC1>[CH2:33]([O:40][C:31]([NH:28][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:16])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 4661317(R)-Tetrahydro-3-furoic acid

生成物 1

HCID 21864525Benzyl oxolan-3-ylcarbamate収率 51.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 3-tetrahydrofuroic acid (3.5 gm, 30 mmol), diphenylphosphorylazide (6.82 ml, 32 mmol), triethylamine (5 ml, 36 mmol) in dioxane (35 ml) was stirred at RT for 20 min then heated in a 100° C. oil bath under dry nitrogen for 2 hours. Benzyl alcohol (4.7 ml, 45 mmol) was added, and continued heating at 100° C. for 22 hours. The mixture was cooled, filtered from a white precipitate and concentrated. The residue was dissolved in 2N HCI and extracted twice using EtOAc. The extracts were washed with water, sodium bicarbonate, brine dried over MgSO4, and then concentrated to an oil which solidifies upon standing. The oil was chromatographed (30% to 60% EtOAc/Hex) to give 3.4 g of an oil (51%).

後処理

  1. temperaturethen heated in a 100° C. oil bath under dry nitrogen for 2 hours
  2. temperaturecontinued heating at 100° C. for 22 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered from a white precipitate
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in 2N HCI
  7. extractionextracted twice using EtOAc
  8. washThe extracts were washed with water, sodium bicarbonate, brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated to an oil which
  11. customThe oil was chromatographed (30% to 60% EtOAc/Hex)

出典と根拠

ORDレコード
ord-c15d9c2a8d7d4793951ee2e3b6757706
出典データセット
uspto-grants-1998_08
特許番号
US05789416

反応ノート

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