Carbon Dioxide → HCID 86695168, compound

HRID 1504013Notes

Reaction equation

HRID 1504013 reaction equation
[Cl:1][C:2]1[C:3]2[C:4]3[CH2:5][CH:6]([CH2:15][CH2:16][OH:17])[CH2:7][CH2:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1.C(=O)=O>CO>[Cl:1][C:2]1[C:3]2[C:4]3[CH2:5][C@@H:6]([CH2:15][CH2:16][OH:17])[CH2:7][CH2:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 86695166HCID 86695166, compound

Product 1

HCID 86695168HCID 86695168, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Purification of compound 154.1. The racemic 2-[3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]ethan-1-ol (2.20 g, 8.19 mmol, 1.00 equiv) was resolute by chiral preparative SFC under the following conditions: column: Chiralpak IA, 2*25 cm, 5 um; mobile phase, CO2 (80%), methanol (domestic, 20%); flow rate: 40 g/min; UV detection at 254 nm. The fractions of the first peak to elute (tR=9.28 min) were collected and evaporated under reduced pressure to give the desired 2-[(12S)-3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]ethan-1-ol (compound 154.1, stereochemistry unconfirmed, 660 mg) as an off-white solid with 100% ee. The fractions of the second peak to elute (tR=10.53 min) were concentrated to give 2-[(12R)-3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]ethan-1-ol (compound 154.2, stereochemistry unconfirmed, 790 mg) as an off-white solid with 98.5% ee.

Workup

  1. customPurification of compound 154.1
  2. washThe fractions of the first peak to elute (tR=9.28 min)
  3. customwere collected
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3cc1bc5dedd54972a09cc9a3b1b30b4c
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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