Chlorotrimethylsilane → D-2-Aminohexano-6-lactam

HRID 60068

Reaction equation

HRID 60068 reaction equation
Cl.[NH2:2][C@@H:3]([C:9]([OH:11])=O)[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].C[Si](C)(C)N[Si](C)(C)C.Cl[Si](C)(C)C>C1(C)C(C)=CC=CC=1>[NH2:2][C@@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1=[O:11]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 13838HexamethyldisilazaneHCID 81691Lysine hydrochloride, D-

Product 1

HCID 439823D-2-Aminohexano-6-lactam

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (R)-lysine HCl salt (100 g, 0.68 mol) in xylene (1 L) was added hexamethyldisilazane (1000 mL, 4.76 mol) and chlorotrimethylsilane (10 mL, 78.8 mmol). The mixture was heated to 120° C. for 24 h, then to 180° C. for 48 h. The solvent was then removed under reduced pressure and the crude material was purified by column chromatography (20:1 to 10:1 CH2Cl2/MeOH) to afford (R)-3-aminoazepan-2-one (I-1a).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe crude material was purified by column chromatography (20:1 to 10:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-6d4b5949406f44f498638a066d6521b7
Source dataset
uspto-grants-2016_09
Patent number
US09440957B2

Linked notes

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