HCID 20355557、化合物 → 3-(Hydroxymethyl)-1lambda6,2-thiazolidine-1,1-dione

HRID 225422ノート

反応式

HRID 225422 の反応式
C([O:8][CH2:9][CH:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[NH:11]1)C1C=CC=CC=1>C(OC(C)=O)(C)C.[Pd]>[OH:8][CH2:9][CH:10]1[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[NH:11]1

参加物

4

反応物 1

HCID 20355557HCID 20355557、化合物

生成物 1

HCID 203555593-(Hydroxymethyl)-1lambda6,2-thiazolidine-1,1-dione収率 67%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 7915Isopropyl Acetate溶媒2 回

実験手順

Dioxide 7 (40 g, 0.17 mol) was placed in the glass liner within a 2 L Parr hydrogenator and dissolved in a mixture of IMS (150 ml) and iPrOAc (150 ml). A suspension of 5% palladium on carbon (Johnson Matthey type 392, 18 g) in iPrOAc (50 mL) was added and the suspension stirred under a hydrogen atmosphere of 70 psi for 3 days. After this time an NMR IPC was carried out that showed approx 15% benzylated material still present. After a further 4 days the reaction was 94% complete and it was decided to stop the hydrogenolysis. The palladium catalyst was filtered under nitrogen on a bed of celite, which was subsequently washed with IMS (250 mL) and iPrOAc (250 mL). The filtrate and washings were concentrated to give the crude product as an oil (26.26 g). The oil was purified by flash column chromatography (silica gel, DCM/methanol (9:1)) yielding 16.65 g (67%) of the hydroxyl-dioxide 8 as a white solid.

後処理

  1. additionwas added
  2. waitAfter a further 4 days the reaction was
  3. filtrationThe palladium catalyst was filtered under nitrogen on a bed of celite, which
  4. washwas subsequently washed with IMS (250 mL) and iPrOAc (250 mL)
  5. concentrationThe filtrate and washings were concentrated
  6. customto give the crude product as an oil (26.26 g)
  7. customThe oil was purified by flash column chromatography (silica gel, DCM/methanol (9:1))

出典と根拠

ORDレコード
ord-2a786ed7b2e54904bcebd00e19146709
出典データセット
uspto-grants-2009_07
特許番号
US07557095B2

反応ノート

読み込み中…