Trityl chloride → HCID 69284943, compound

HRID 2249924Notes

Reaction equation

HRID 2249924 reaction equation
[OH:1][CH2:2][C@H:3]1[NH:8][C:7](=[O:9])[CH2:6][CH2:5][CH2:4]1.[C:10](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:10]([O:1][CH2:2][C@H:3]1[NH:8][C:7](=[O:9])[CH2:6][CH2:5][CH2:4]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 10855475(S)-6-(Hydroxymethyl)piperidin-2-one

Product 1

HCID 69284943HCID 69284943, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-39 (5.85 g, 45.3 mmol), trityl chloride (16.04 g, 57.5 mmol), i-Pr2NEt (11.6 mL, 66.6 mmol) and DMAP (0.527 g, 4.31 mmol) in DMF (21 mL) was stirred at r.t for 3 days. Reaction mixture was separated between brine (80 mL) and water (80 mL). The aqueous layer was extracted with AcOEt (4×80 mL). Combined organic solutions were washed with brine, dried (MgSO4), concentrated and separated by SGC with hexane:AcOEt (in gradient, up to 40% AcOEt) to afford (S)-40 as a foam; yield 12.20 g (73%). 1H NMR (250 MHz, CDCl3) δ 1.16-1.34 (m, 1H), 1.58-1.90 (m, 3H), 2.17-2.31 (m, 1H), 2.33-2.47 (m, 1H), 2.94 (t, J=9.1 Hz, 1H), 3.23 (dd, J=9.1, 3.1 Hz, 1H), 3.56-3.68 (m, 1H), 6.21 (s, 1H), 7.21-7.45 (m, 15H).

Workup

  1. customReaction mixture
  2. customwas separated between brine (80 mL) and water (80 mL)
  3. extractionThe aqueous layer was extracted with AcOEt (4×80 mL)
  4. washCombined organic solutions were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customseparated by SGC with hexane
  8. customAcOEt (in gradient, up to 40% AcOEt) to afford (S)-40 as a foam

Sources & evidence

ORD record
ord-0edda2956fc84b75a170ce3f0d45f860
Source dataset
uspto-grants-2008_01
Patent number
US07314940B2

Reaction notes

Loading…